(a)
Interpretation:
The structure of six-membered cyclic hemiacetal formed by 5-hydroxyhexanal should be drawn.
Concept Introduction:
Hemiacetal is a molecule formed by the addition of an alcohol to an

Answer to Problem 63P
Explanation of Solution
Reaction of the aldehyde group and the hydroxyl group forms a six-membered cyclic hemiacetal.
Therefore, the structure hemiacetal formed from 5-hydroxyhexanalis as follows:
(b)
Interpretation:
The number of possible stereoisomers of 5-hydroxyhexanal should be determined.
Concept Introduction:
Stereoisomers are the compounds that are differ only in the spatial arrangements of their atoms. For a molecule with n stereoisomers, a maximum of

Answer to Problem 63P
5-hydroxyhexanal has 2 stereoisomers.
Explanation of Solution
For a molecule with n stereoisomers, a maximum of
In 5-hydroxyhexanal, there is one stereocenter.
Therefore, number of stereoisomers can be calculated as follows:
Thus, number of stereoisomers will be 2.
(c)
Interpretation:
The number of possible stereoisomers of hemiacetal of 5-hydroxyhexanal should be calculated.
Concept Introduction:
Stereoisomers are the compounds that are differ only in the spatial arrangements of their atoms. For a molecule with n stereoisomers, a maximum of

Answer to Problem 63P
Hemiacetal of 5-hydroxyhexanal has 4 stereoisomers.
Explanation of Solution
For a molecule with n stereoisomers, a maximum of
In hemiacetal of 5-hydroxyhexanal, there are two stereo centres.
Therefore, number of stereoisomers can be calculated as follows:
Thus, number of stereoisomers are 4.
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Chapter 16 Solutions
Introduction to General, Organic and Biochemistry
- Predict the organic product that forms in the reaction below: H + гон OH H+ H+ ☑ O Note: You may assume you have an excess of either reactant if the reaction requires more than one of those molecules to form the product. In the drawing area below, draw the skeletal ("line") structure of the missing organic product X. Explanation Check Click and drag to start drawing a structure. S 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Centearrow_forwardIn the analysis of Mg content in a 25 mL sample, a titration volume of 5 mL was obtained using 0.01 M EDTA. Calculate the Mg content in the sample if the Ca content is 20 ppmarrow_forwardPredict the organic products that form in the reaction below: H. H+ + OH H+ Y Note: You may assume you have an excess of either reactant if the reaction requires more than one of those molecules to form the products. In the drawing area below, draw the skeletal ("line") structures of the missing organic products X and Y. You may draw the structures in any arrangement that you like, so long as they aren't touching. Explanation Check Click and drag to start drawing a structure. G X C © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Access +arrow_forward
- 111 Carbonyl Chem Choosing reagants for a Wittig reaction What would be the best choices for the missing reagents 1 and 3 in this synthesis? 1. PPh3 3 1 2 2. n-BuLi • Draw the missing reagents in the drawing area below. You can draw them in any arrangement you like. Do not draw the missing reagent 2. If you draw 1 correctly, we'll know what it is. • Note: if one of your reagents needs to contain a halogen, use bromine. Explanation Check Click and drag to start drawing a structure. × ©2025 McGraw Hill LLC. All Rights Reserved. Terms of Usearrow_forwardA student proposes the transformation below in one step of an organic synthesis. There may be one or more reactants missing from the left-hand side, but there are no products missing from the right-hand side. There may also be catalysts, small inorganic reagents, and other important reaction conditions missing from the arrow. • Is the student's transformation possible? If not, check the box under the drawing area. . If the student's transformation is possible, then complete the reaction by adding any missing reactants to the left-hand side, and adding required catalysts, inorganic reagents, or other important reaction conditions above and below the arrow. • You do not need to balance the reaction, but be sure every important organic reactant or product is shown. + T X O O лет-ле HO OH HO OH This transformation can't be done in one step.arrow_forwardDetermine the structures of the missing organic molecules in the following reaction: X+H₂O H* H+ Y OH OH Note: Molecules that share the same letter have the exact same structure. In the drawing area below, draw the skeletal ("line") structures of the missing organic molecules X and Y. You may draw the structures in any arrangement that you like, so long as they aren't touching. Click and drag to start drawing a structure. X Sarrow_forward
- Predict the major products of this organic reaction. If there aren't any products, because nothing will happen, check the box under the drawing area instead. No reaction. HO. O :☐ + G Na O.H Click and drag to start drawing a structure. XS xs H₂Oarrow_forwardWhat are the angles a and b in the actual molecule of which this is a Lewis structure? H H C H- a -H b H Note for advanced students: give the ideal angles, and don't worry about small differences from the ideal groups may have slightly different sizes. a = b = 0 °arrow_forwardWhat are the angles a and b in the actual molecule of which this is a Lewis structure? :0: HCOH a Note for advanced students: give the ideal angles, and don't worry about small differences from the ideal that might be caused by the fact that different electron groups may have slightly different sizes. a = 0 b=0° Sarrow_forward
- Determine the structures of the missing organic molecules in the following reaction: + H₂O +H OH O OH +H OH X Note: Molecules that share the same letter have the exact same structure. In the drawing area below, draw the skeletal ("line") structure of the missing organic molecule X. Click and drag to start drawing a structure.arrow_forwardIdentify the missing organic reactant in the following reaction: x + x O OH H* + ☑- X H+ O O Х Note: This chemical equation only focuses on the important organic molecules in the reaction. Additional inorganic or small-molecule reactants or products (like H₂O) are not shown. In the drawing area below, draw the skeletal ("line") structure of the missing organic reactant X. Click and drag to start drawing a structure. Carrow_forwardCH3O OH OH O hemiacetal O acetal O neither O 0 O hemiacetal acetal neither OH hemiacetal O acetal O neither CH2 O-CH2-CH3 CH3-C-OH O hemiacetal O acetal CH3-CH2-CH2-0-c-O-CH2-CH2-CH3 O neither HO-CH2 ? 000 Ar Barrow_forward
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